6 Birthday Celebrations - HELP!!!

So we're planning a gift for a really good friend who's turning 40. He lives in the South End and is single; we (the givers) are six couples who live in the burbs and will be coming into the city for six different dinners (the gift). Each couple is giving a gift certificate to him at a different place, and we'll make up a calendar of dates, so that the final gift is 6 months worth of dinners, for all 13 of us, at six different locations. Did I confuse?

But now, of course, I'm stumped. He's not a crazy-adventurous guy, and we'd need places that can accomodate a large (and loud) group, but good food is paramount. Not necessarily crazy-expensive food (although we dont want cheap), but it's all about the overall experience.

Do they need to be located in the SE (ie, is someone also going to give him the gift of picking him up and returning him home if outside the 'hood?)? The reason I ask is that he probably is quite familiar with the restaurants in the SE and Back Bay, and this could be an opportunity for him to go elsewhere (just just Boston, Cambridge, Somerville and Brookline but also Quincy, Arlington, Malden, et cet.) for a change of pace. That would expand your options mightily.

I assume he would already be very familiar with the larger-size SE standbys like Union, Banc and Rocca. Though the Theatre District, Chinatown and the NE have many options for noisy large parties, you suburbanites would not like dealing with the parking there. So I am omitting those 'hoods for that practical reason, though blu at the (new) Ritz would also be fine (I recall attending a loud birthday for someone there a few years ago, and it was great).

Estragon would be my choice of a moderately adventurous (but not too) place in the SE that would fit a party like yours. They offer very fine (if not necessarily immortal) mains and tapas, without the scene or attitude of Toro.